Chester Holidays from £492

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Your Chester Holiday

The best way to experience this vibrant city is with a custom-made Chester holiday package. Stay in the neighbourhood of Essex Village, which is good for walking, hiking and views or choose someplace else — our packages are all about you. Essex Steam Train, Goodspeed Opera House and Essex Island Marina are just some of the many sights you'll want to check out during your trip to Chester. Check out Expedia's extensive range of travel options and begin planning your perfect holiday to Chester now.

The Latest Chester Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
per person
4 Sept - 8 Sept
found 1 day ago
Return flight included
London (LGW) to New Haven (HVN)
7.8/10 Good! (974 reviews)
This is a great place to stay with an outstanding location in Old Saybrook right on RT 1. Great breakfast cafe right across the street.

Reviewed on 24 Jun 2025

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
per person
4 Sept - 8 Sept
found 1 day ago
Return flight included
London (LGW) to New Haven (HVN)
9.4/10 Exceptional! (1,005 reviews)
One of the best location on the planet

Reviewed on 23 Jun 2025

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast

4 out of 5
Old Saybrook Center
per person
4 Sept - 8 Sept
found 1 day ago
Return flight included
London (LGW) to New Haven (HVN)
9.4/10 Exceptional! (16 reviews)
We loved the convenient location and beautiful historic building, but we were very disappointed in the level of cleanliness (a layer of dust on shelves and fireplace, cobwebs under furniture). There were some other issues (loose shower head, broken coffee maker). There's no one on site to address in person. It's a lovely place, but needs some attention. For the price, it should be better! :(

Reviewed on 1 May 2025

The Captain Stannard

The Captain Stannard

3 out of 5
Westbrook Center
per person
4 Sept - 8 Sept
found 1 day ago
Return flight included
London (LGW) to New Haven (HVN)
9.6/10 Exceptional! (227 reviews)
Very nice place and the owners are super people and treat their customers very well! I loved it here and would definitely stay here again!

Reviewed on 2 Jun 2025

The Niantic Inn

The Niantic Inn

2 out of 5
per person
4 Sept - 8 Sept
found 1 day ago
Return flight included
London (LGW) to New Haven (HVN)
9.2/10 Wonderful! (96 reviews)
Everything was great .Location is perfect to shop and dine. Only issue was garbage was left in stairwells overnight

Reviewed on 2 May 2025

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
1,550
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Harveys Beach, Goodspeed Opera House and Devils Hopyard State Park

Our pick of the best Chester Hotel Deals

Motel 6 New Haven - Branford, CT
Motel 6 New Haven - Branford, CT
2 out of 5
320 E Main St, Branford, CT
Stay at this motel in Branford. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their reviews. ...
6.8/10 (1,004 reviews)
"Inexpensive, clean, and available on very short notice after a minor travel interruption. We were quite satisfied with the accommodations."

Reviewed on 18 Jun 2025

Motel 6 New Haven - Branford, CT
Mohegan Sun
Mohegan Sun
4.5 out of 5
1 Mohegan Sun Boulevard, Montville, CT
Stay at this 4.5-star luxury resort in Montville. Enjoy free Wi-Fi, free parking and 2 indoor pools. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,910 reviews)
"Everyone had a wonderful time. The room was very comfortable."

Reviewed on 20 Jun 2025

Mohegan Sun
Hyatt Place Uncasville - Casino Area
Hyatt Place Uncasville - Casino Area
3 out of 5
2049 Norwich, New London Turnpike, Montville, CT
Stay at this 3-star business-friendly hotel in Montville. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (2,439 reviews)
"Clean amd convenient to casino"

Reviewed on 21 Jun 2025

Hyatt Place Uncasville - Casino Area
See all 1,064 properties in Chester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Chester travel package cost?
Maybe less than you imagined --- from a low £492, actually! By bundling flights, hotels and car rentals into a custom-built package, your trip to Chester is only clicks away.
If I'm not able to travel, can I cancel my Chester travel package?
You can. We totally understand that even the best-laid plans can fail, so we're here to help if you have to make changes to your Chester travel package. It may be possible to cancel or amend your itinerary at no cost if you've booked in the last 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Head to our Customer Service Portal for further information. Also, be sure to check your itinerary for the nitty-gritty on change fees.
How do I get a cheap travel package to Chester?
Combine your bookings with Expedia to save big on your next trip. With over 550 air carriers and 1,000,000 properties across the globe, your Chester travel package can be tailored exactly to suit your budget. With all that extra money, why not include one or more interesting tours and activities? It's an easy way to unlock even more bargains. That holiday you've always dreamed of in Chester is much closer than you thought!
Does Expedia offer Book Now, Pay Later Chester holidays?
Your bank balance shouldn't prevent you from taking a holiday, so Expedia has worked out a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book an incredible getaway without eating away at your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your break. Check out these flexible payment options:
  • Pay monthly holidays: If paying small amounts each month is something that would work for you, Klarna offers just that! Paying in convenient monthly instalments will make your holiday dreams come true.
  • Pay in instalments holidays: If you'd prefer to pay off your getaway across multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Pressing the "book now" button is easier with this option. Just put down a small deposit on your booking and then start working on your travel itinerary.

Where should I stay in Chester?
With loads to explore in Chester, we suggest you stay near its attractions. Norma Terris Theatre, Chester Creek Marina and Plattwood Park are some good ones to add to your itinerary.
What are the top hotels in Chester?
Saybrook Point Resort & Marina and Pier Blue Inn Old Saybrook - Essex are among the most popular hotels in Chester. Why not check out the amenities and facilities at each and then make a decision?
How far in advance should I book my Chester holiday?
Search Expedia to compare international flights as soon as you know your travel dates. You can generally purchase a ticket up to a year prior to departure. If you can't find your preferred air carrier, or you're booking late, fear not. Cheap tickets to Chester sometimes appear a few weeks before the date of departure.
What does an Expedia Chester travel package include?
From hotels and flights to rental cars, Expedia can help you put together a Chester package that's ideal for you. Heading away for a few weeks? Check out a rental car, flight and hotel bundle. If you're taking a short break, a flight and hotel deal may suit you better. Experiences can also be added once you've made your booking. Our packages make it a breeze to save and plan.
What should I know before booking a Chester travel package?
Tailor deals that fit your budget with an Expedia package. Hotels, flights, rental cars --- we've got everything you need to plan your getaway. You'll save a packet just for bundling your bookings. Whether you're going on a snow and ski adventure or drinking cocktails on a beach, your ideal getaway is only clicks away.
Can I choose my airline with a Chester Expedia travel package?
Yes, so take your pick! We have access to over 550 airlines around the world, so you can design your Chester getaway according to your style and budget.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.